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Dichloromethane → Ethyl 6-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

HRID 335314
ノート
印刷プレビュー

反応式

HRID 335314 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=1.[CH3:16][N:17]1[C:21](B2OC(C)(C)C(C)(C)O2)=[CH:20][CH:19]=[N:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>COCCOC.O.CO.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:16][N:17]1[C:21]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([N:8]=[CH:9][C:10]=3[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=2)=[CH:20][CH:19]=[N:18]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 4

HCID 6344Dichloromethane3 回HCID 10796Cesium carbonateHCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2 回HCID 12208504Ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate

生成物 1

HCID 71283198Ethyl 6-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridine-3-carboxylate

試薬・触媒・溶媒 5

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
3 回
HCID 887Methanol溶媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture comprising ethyl 6-bromopyrazolo[1,5-a]pyridine-3-carboxylate (1.5 g, 5.57 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.218 g, 5.85 mmol), cesium carbonate (7.26 g, 22.30 mmol) and PdCl2(dppf).CH2Cl2 adduct (91 mg, 0.111 mmol) in DME (10 ml) and water (4.00 ml) was heated using microwave radiation at 70° C. for 1 hr. Further PdCl2(dppf).CH2Cl2 adduct (91 mg, 0.111 mmol) was added and the mixture was heated at 80° C. for 1 hr. 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.218 g, 5.85 mmol) and PdCl2(dppf).CH2Cl2 adduct (91 mg, 0.111 mmol) were added and heating continued at 100° C. for 3 hrs. The mixture was diluted with 10% MeOH in EtOAc (200 ml) and washed with sat. NaHCO3. The organic solvent was removed under vacuum and azeotroped with toluene. The resulting solid was loaded onto silica and purified by chromatography eluting with 0-100% EtOAc in iso-hexane to afford the title compound;

後処理

  1. customat 70° C.
  2. customfor 1 hr
  3. temperatureheating
  4. washwashed with sat. NaHCO3
  5. customThe organic solvent was removed under vacuum
  6. customazeotroped with toluene
  7. custompurified by chromatography
  8. washeluting with 0-100% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-a51e8a8797644202b84ed8ddc75e957f
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883819B2

反応ノート

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